Aziridine → HCID 21428829, compound

HRID 437618

Reaction equation

HRID 437618 reaction equation
[NH:1]1[CH2:3][CH2:2]1.C(=O)([O-])O.[Na+].[OH:9][C:10]1[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=1[C:12](Cl)=[O:13].[OH-].[Na+]>O.ClC(Cl)Cl>[OH:9][C:10]1[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=1[C:12]([N:1]1[CH2:3][CH2:2]1)=[O:13]

Participants

7

Reactant 4

HCID 9033AziridineHCID 14798Sodium HydroxideHCID 74041Salicyloyl chlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 21428829HCID 21428829, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Conditions

Temperature
-5 °C

Procedure

To 690 parts of a solution of aziridine in water 0.875M are added 42 parts of sodium hydrogen carbonate while cooling in an ice-salt bath at -5° C. While stirring vigorously, there is added dropwise, during a 30 minutes period, a solution of 78.8 parts of 2-hydroxybenzoyl chloride in 150 parts of trichloromethane at a temperature below 5° C. The reaction mixture is allowed to reach 25° C while stirring, and a diluted sodium hydroxide solution is added to pH 8. The product is extracted three times with trichloromethane. The combined extracts are washed three times with water, dried, filtered and evaporated, yielding 56 parts of 1-(2-hydroxybenzoyl)aziridine as a residue.

Workup

  1. additionthere is added dropwise, during a 30 minutes period
  2. customat a temperature below 5° C
  3. customto reach 25° C
  4. stirringwhile stirring
  5. extractionThe product is extracted three times with trichloromethane
  6. washThe combined extracts are washed three times with water
  7. customdried
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-d831ca452c1d40e9aa3a624c99eea2a9
Source dataset
uspto-grants-1977_06
Patent number
US04031226

Linked notes

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